N-acetyl-4-O-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-α-D-muramic acid, 6-acetate, 1-(benzyl hexadecyl phosphate)

Base Information

Chemical Name:N-acetyl-4-O-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-α-D-muramic acid, 6-acetate, 1-(benzyl hexadecyl phosphate)
CAS No.:1380522-17-7
Molecular Formula:C₅₀H₇₉N₂O₂₀P
Molecular Weight:1059.15
Hs Code.:

Synonyms:N-acetyl-4-O-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-α-D-muramic acid, 6-acetate, 1-(benzyl hexadecyl phosphate)

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Chemical Property of N-acetyl-4-O-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-α-D-muramic acid, 6-acetate, 1-(benzyl hexadecyl phosphate)

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Technology Process of N-acetyl-4-O-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-α-D-muramic acid, 6-acetate, 1-(benzyl hexadecyl phosphate)

There total 15 articles about N-acetyl-4-O-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-α-D-muramic acid, 6-acetate, 1-(benzyl hexadecyl phosphate) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

: 1380522-11-1
C₅₈H₈₇N₂O₂₂PS

: 1380522-17-7
N-acetyl-4-O-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-α-D-muramic acid, 6-acetate, 1-(benzyl hexadecyl phosphate)

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃; for 1.5h;
DOI:10.1021/ja302099u

Reference yield:

: 914642-50-5
benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

: 1380522-17-7
N-acetyl-4-O-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-α-D-muramic acid, 6-acetate, 1-(benzyl hexadecyl phosphate)

Guidance literature:: Multi-step reaction with 6 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / Molecular sieve

2: zinc(II) chloride / acetic acid

3: palladium 10% on activated carbon; hydrogen / methanol / 760.05 Torr

4: 1H-tetrazole / acetonitrile / 12 h / 20 °C / Inert atmosphere

5: dihydrogen peroxide / water; acetonitrile / 0.58 h / -78 - 20 °C

6: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / 0 - 20 °C

With 1H-tetrazole; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) chloride; In methanol; dichloromethane; water; acetic acid; acetonitrile; 1: Schmidt reaction;
DOI:10.1021/ja302099u

Reference yield:

: 917029-93-7
benzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

: 1380522-17-7
N-acetyl-4-O-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-α-D-muramic acid, 6-acetate, 1-(benzyl hexadecyl phosphate)

Guidance literature:: Multi-step reaction with 4 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 760.05 Torr

2: 1H-tetrazole / acetonitrile / 12 h / 20 °C / Inert atmosphere

3: dihydrogen peroxide / water; acetonitrile / 0.58 h / -78 - 20 °C

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / 0 - 20 °C

With 1H-tetrazole; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ja302099u